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- Publisher Website: 10.1016/j.checat.2024.100999
- Scopus: eid_2-s2.0-85192823336
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Article: A versatile cobalt catalyst for highly enantioselective hydrogenation of carbonyl compounds
Title | A versatile cobalt catalyst for highly enantioselective hydrogenation of carbonyl compounds |
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Authors | |
Keywords | asymmetric hydrogenation chiral drugs cobalt dynamic kinetic resolution ketoamide ketone mechanistic insight SDG9: Industry, innovation, and infrastructure |
Issue Date | 16-May-2024 |
Publisher | Cell Press |
Citation | Chem Catalysis, 2024, v. 4, n. 5 How to Cite? |
Abstract | A general base metal catalytic system for asymmetric hydrogenation of different types of carbonyl compounds has rarely been reported. Here, we describe the development of a versatile Co/BPE system for the asymmetric hydrogenation of both α-ketoamides and aryl alkyl ketones that enable fast access to various chiral α-hydroxy amides and secondary alcohols in excellent yields and enantioselectivities (up to 98% yield and 99:1 enantiomeric ratio [er]) under base- and additive-free conditions. More importantly, cobalt-catalyzed diastereo- and enantioselective hydrogenation of α-substituted β-ketoamides has been achieved for the first time under a dynamic kinetic resolution (DKR) process using the same system. The synthetic potential has been demonstrated through reaction scale-up, product derivatization, and synthesis of various key intermediates for chiral drugs. Mechanistic studies support a new Co(II) instead of a Co(II)/Co(0) catalytic cycle involving hydride transfer and H2 splitting processes, in which the oxidation state of cobalt remains unchanged. |
Persistent Identifier | http://hdl.handle.net/10722/346485 |
ISSN | 2023 SCImago Journal Rankings: 3.455 |
DC Field | Value | Language |
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dc.contributor.author | Du, Xiaoyong | - |
dc.contributor.author | Zhang, Yao | - |
dc.contributor.author | Yang, Tilong | - |
dc.contributor.author | Xiao, Ye | - |
dc.contributor.author | He, Jian | - |
dc.contributor.author | Chung, Lung Wa | - |
dc.contributor.author | Chen, Gen Qiang | - |
dc.contributor.author | Zhang, Xumu | - |
dc.date.accessioned | 2024-09-17T00:30:54Z | - |
dc.date.available | 2024-09-17T00:30:54Z | - |
dc.date.issued | 2024-05-16 | - |
dc.identifier.citation | Chem Catalysis, 2024, v. 4, n. 5 | - |
dc.identifier.issn | 2667-1107 | - |
dc.identifier.uri | http://hdl.handle.net/10722/346485 | - |
dc.description.abstract | A general base metal catalytic system for asymmetric hydrogenation of different types of carbonyl compounds has rarely been reported. Here, we describe the development of a versatile Co/BPE system for the asymmetric hydrogenation of both α-ketoamides and aryl alkyl ketones that enable fast access to various chiral α-hydroxy amides and secondary alcohols in excellent yields and enantioselectivities (up to 98% yield and 99:1 enantiomeric ratio [er]) under base- and additive-free conditions. More importantly, cobalt-catalyzed diastereo- and enantioselective hydrogenation of α-substituted β-ketoamides has been achieved for the first time under a dynamic kinetic resolution (DKR) process using the same system. The synthetic potential has been demonstrated through reaction scale-up, product derivatization, and synthesis of various key intermediates for chiral drugs. Mechanistic studies support a new Co(II) instead of a Co(II)/Co(0) catalytic cycle involving hydride transfer and H2 splitting processes, in which the oxidation state of cobalt remains unchanged. | - |
dc.language | eng | - |
dc.publisher | Cell Press | - |
dc.relation.ispartof | Chem Catalysis | - |
dc.rights | This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License. | - |
dc.subject | asymmetric hydrogenation | - |
dc.subject | chiral drugs | - |
dc.subject | cobalt | - |
dc.subject | dynamic kinetic resolution | - |
dc.subject | ketoamide | - |
dc.subject | ketone | - |
dc.subject | mechanistic insight | - |
dc.subject | SDG9: Industry, innovation, and infrastructure | - |
dc.title | A versatile cobalt catalyst for highly enantioselective hydrogenation of carbonyl compounds | - |
dc.type | Article | - |
dc.identifier.doi | 10.1016/j.checat.2024.100999 | - |
dc.identifier.scopus | eid_2-s2.0-85192823336 | - |
dc.identifier.volume | 4 | - |
dc.identifier.issue | 5 | - |
dc.identifier.eissn | 2667-1093 | - |
dc.identifier.issnl | 2667-1093 | - |